


Sharing is Caring

by quirkybookworm



Category: Teen Wolf (TV)
Genre: Anal Sex, Consensual Infidelity, Cuckolding, Dom/sub Undertones, F/M, Jealousy, M/M, Multi, Open Relationships, Orgasm Control, Polyamory Negotiations, Voyeurism, mentions of somnophilia, mentions of watersports
Language: English
Status: Completed
Published: 2017-01-04
Updated: 2017-01-06
Packaged: 2018-09-14 17:10:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 12,759
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9195569
Author URL: https://archiveofourown.org/users/quirkybookworm/pseuds/quirkybookworm
Summary: Stiles develops a new kink, and Derek is surprisingly into it.





	1. Chapter 1

**Author's Note:**

> I can't believe this is my first time posting a TW fic, because TW is probably the fandom that I'm most apart of. 
> 
> As a warning: this fic contains mentions of various kinks, as well as kink negotiations. The only kink explicitly explored in this fic is Stiles' cuckold kink, however the following are mentioned: watersports, public sex, roleplaying, somnophilia, bondage, as well as a few others. 
> 
> Also, this fic was unbeta'd and written largely in the wee hours of the morning so bare that in mind.

Stiles and Derek had a very healthy, very active, sex life which wasn’t really a surprise considering that they were both young men with strong libidos. And, the fact that they both had a kinky side that helped keep things new and exciting, didn’t hurt anything, either, and they were both surprisingly open to whatever the other wanted to try. Well, Derek was surprisingly open, Stiles was just open. He was Stiles, he could get off to just about anything, especially since the just about anything was happening with Derek Fucking Hale. So, Derek wanted to tie him up on a Wednesday afternoon after Stiles got home from class? Stiles will go get the rope. Derek wanted to try roleplaying? Well, come here, Daddy. Derek wanted to fuck him in his sleep? Awesome. Derek wanted to fuck him in the woods in his beta form? Stiles was down with that. Derek wanted to pee on Stiles in the shower? Cool, just don’t accidently get it on the floor, please. And, Derek was just as willing to fulfill Stiles’ fantasies. Like the time that Stiles asked Derek to fuck him in the dressing room at the mall, or when Stiles asked Derek if he’d let him top, or when Stiles asked Derek to rim him, or the hundred plus other things that Stiles had asked Derek to do.  


Their little arrangement worked well. Stiles went to school, Derek worked, Stiles vacuumed their home, Derek dusted it, Stiles washed the dishes, Derek dried the dishes. There was a natural ebb and flow to their relationship that was kind of amazing. That wasn’t to say that there were never problems, though, because there definitely were. Stiles was still as hyperactive and spastic as he was in high school, the immense worry that he’d had for his father had seemingly shifted over onto Derek since they moved in together, and he had still not developed much of a filter. And, Derek was still Derek. No matter how well things were going between him and Stiles, that didn’t change what had happened to him in his past, and some days those demons would catch up to him and he would go off on his own for days at time to brood and mope and hide from the world. Which would ignite Stiles’ worry streak, which would then start an argument because they were both tired and frustrated, Stiles because why the fuck does he do that when he knows how Stiles worries? Is a simple text really too much to ask for?, and Derek because for fucks sake, he’s a grown man, he can take care of himself. He has been since the fire. If he needs a few days, then he’ll take a few days, Stiles needs to understand that Derek knows what’s best for Derek.  


So, no, things weren’t this perfect fairytale, but they were good. 29 days out of the month, they worked well together, they got along, and as for the other day or two, well, they had their whole lives to work on that.

Derek was over at Isaac’s for a beer and football night, and to give Stiles some quiet time to study. Not that it took Stiles the duration of a football game to study, but Stiles was happy to pretend that it did if that made Derek go spend more time with Isaac. Isaac and Derek had had a bit of a falling out when Isaac left after Allison died, and they were just starting to repair that, so they needed all the excuses to hang out together that they could get.  


So, Stiles was home alone with nothing to do and it’s not his fault that internet porn is a thing, that’s just there, for free. It’s also not his fault that his favorite website was advertising a new category, and it’s not his fault that he’s a naturally curious person who wanted to find out what ‘cuckold’ meant. Nor was it his fault that his dick really seemed to like ‘cuckold’ porn. What might’ve been his fault was that he spent the next several hours scouring the internet for cuckold porn. Not just any kind of cuckold porn, though. He tried, fruitlessly, to find fics or videos of a couple like him and Derek. When he couldn’t, he closed his laptop, sprawled out in the bed that he and Derek shared and just let his mind go to a place that he’d never thought he’d feel anything but jealousy when he went there, but he did. He imagined Derek coming home from a night out, with a pretty girl with long blonde hair, and curves, and he imagined himself waiting up patiently. Maybe hiding in a darkened corner of their room as Derek kissed her, as Derek fucked her, in their bed. And, then Stiles comes harder than he’s ever come in his whole life. After, he feels the jealousy that he’d imagined he’d feel when he first went there in his head, he feels dirty, and ashamed, but he still feels turned on when he thinks about it, too. His dick, soft and sensitive, now, gives a twitch of interest at the idea even though he just came a few minutes before, and it’s then that he knows this wasn’t just a simple, one time only, fantasy.

After the first time, the fantasies take on a life of their own. They get more and more graphic, more and more specific, more and more dirty. It goes from him just sitting in the corner, watching as Derek fucks some random girl, sometimes jerking off as Derek fucks some girl, to watching them fuck and Derek not letting him jack off, and the girls humiliating him. Derek and the girls go from never saying anything, to being very vocal. He pictures Derek being sweet to them, telling them how beautiful they are, how sexy they are, how good they are, and them talking to him, to Stiles, telling him how hot his boyfriend is, how good he is. And, every time Stiles lets himself go there, he gets off over and over and over, again. Overtime, the jealousy he feels stops being an after orgasm thing, and starts being present while he’s fantasizing, but it’s hot, and it makes it better. The jealousy stops curling in his stomach like lead, and starts pooling in his groin like honey. The shame is still there, after, because he knows that it’s probably abnormal to get off on the idea of the love of your life fucking somebody else, but he can’t help it anymore. Nothing else gets him off quite as hard.  


It’s almost 6 months after he first found his newest, and biggest, kink that he tells Derek. They’re sitting on the sofa, watching some stupid crime program that Stiles can’t get into, and, lately, the first place that Stiles’ mind wanders is to his secret little box of cuckold fantasies in the farthest back, darkest, corners of his psyche.

“Do you have some thing for detectives, now?” Derek says to him, arm around Stiles’ shoulders.  


“What? Oh, no. No. Sorry.” Stiles says.  


“Don’t be sorry.” Derek says, other arm reaching down for Stiles’ thigh. His voice goes low, and husky, like it does when he’s trying to get in Stiles’ pants, “Tell me what you were thinking about.”  


“You’ll think I’m crazy.” Stiles says, and he means it.  


“No, I won’t.” Derek bites, softly, at Stiles’ ear, “Tell me.”  


“No, it’s weird, Derek.” Stiles starts to untangle himself from Derek.  


“Hey, wait. What? I thought we didn’t keep these kind of secrets.” Derek’s sitting up on the sofa, now, looking slightly dumbfounded.  


“That was before I became a class A freak.”  


“Stiles, whatever it is, it can’t possibly be weirder than me wanting to pee on you.”  


“It is.” Stiles says, “Trust me.”  


“You trust me.” Derek says, “I’m not saying that I’ll do it, because I don’t know what it is yet, but I am saying that whatever it is isn’t going to make me run away screaming, and it’s not going to make me think less of you – unless you want to kill me, or something.”  


“Oh, yeah, Derek. Totally.” Stiles say with a roll of his eyes, “You caught me. What gets me off is imagining killing you -- slicing your werewolf ass into tiny little pieces.”  


It wasn't funny, or clever, but Derek’s lip turns up at the corner anyway, and the tension is broken.  


Stiles sighs, crosses his arms, “I was thinking about you fucking somebody else.”  


Derek then proceeds to do his best fish imitation.

“I would never cheat on you, Stiles.”  


“I don’t want you to.” Stiles says, sits on the coffee table, “It’s not cheating if we’re both consenting to it.”  


“Why would you want me to…” Derek says, “Stiles, I can’t do the open relationship thing. I can’t share you, I’m not that kind of person.”  


“I don’t expect you to.” Stiles says, and he doesn’t. He gets that Derek’s wolf makes him far too possessive to handle that, and besides, he has no interest in fucking, or getting fucked by, people other than Derek. “Look, I don’t get off on the idea of being with people other than you. I just like the idea of watching.”  


“Watching me. Have sex. With other people.”  


“With girls, yeah.”  


“But not guys?”  


“Not really.”  


“Why not guys, too?”  


“I don’t know.” Stiles says, shrugs his shoulders,“It just doesn’t do much for me. I mean, I’m not opposed to it, but it’s just, not, ya know, as hot. To me.”  


“How long have you been thinking about this?”  


“Months.” Stiles says, honestly.  


“And, you didn’t tell me before now?”  


“I thought you’d think I was nuts.”  


Derek shakes his head, “Nuts? No. A little weird? Yeah.”  


Stiles laughs, because he knows that Derek is joking.  


“C’mon.” Derek stands up, turns off the television, and pulls Stiles’ hand.  


“What?” Stiles says as Derek pulls him into their room.  


“Tell me how it goes. Tell me what you’ve been thinking about for the last few months.”  


“You’re okay with this?” Stiles asks.  


“Yeah, of course. Stiles, you let me pee on you.”  


“Wait,” Stiles says, cock leaking from the mere thought of it, “We’re actually going to do this?”  


“I don’t know if I’m comfortable doing it, for real, but we can think about it.” Derek said against his ear, his hands on Stiles’ hips. “We can talk about it. Tell me. Tell me what you’ve been getting off on all this time. How’d it start?”  


“You were at Isaac’s, and I was done studying, and how can Stiles resist some personal Stiles’ time?”  


Derek made a breathy laughing noise into his ear that sent chills down his spine.  


“I went on a porn site, and they were showing a new category.” Stiles said, quietly, “It was called cuckold, and I was curious so I watched it. I thought I was gonna be jealous, but it was just so fucking hot.”  


Derek started to walk Stiles towards their room, and mumbled, “Mhm.”  


“I always picture you with a pretty blonde, and she’s always confident and bossy. Sometimes, I think about watching it voluntarily, and jerking myself off while you fuck her. Other times, I think about you making me watch.”  


“Making you?” Derek asks as they come to a stop by the foot of their bed, pulling Stiles by the loops on his jeans.  


Stiles felt his face flush a deep pink, “Yeah, like you fucking them even when I say no. Not giving me a choice.”  


Derek grunted, hands moving down to Stiles’ ass, mouth moving to his neck. Stiles wondered if he was actually finding it hot, and not just humoring him.  


That thought goes straight to his dick, the idea of Derek wanting to fuck other people, and maybe it's the shortage of blood to his brain, but it gives him the courage to keep talking, “Sometimes I think about you not letting me get off on it, about it just getting you off, getting them off,”  


Derek's gripping his ass, and lifting him up, before dropping him onto the bed, and Stiles knows he's turned on for real. It rips a groan out of his throat.  


“You want that?” Derek says, no, he groans, into Stiles’ neck, “You want me to fuck them? Cum in them, Stiles?”  


“Yes.” And, it's better. It's so much better than his fantasies, because it's real. This is actual Derek talking to Stiles about fucking other people while Stiles watches.  


Derek usually likes to take his time, but he seems to need this too. He almost rips Stiles’ lucky shirt in his haste to get it off, and Stiles would normally gripe at him for it, but he’s just too turned on to give a damn, really. And, to his credit, Derek doesn’t even complain when Stiles pulls his pants and boxers down at the same time which normally results in an exasperated, ‘Stiles” at the very least, because Derek is a dick who likes to take things slow, and tease Stiles into an early grave.  


Their clothes come off in a rushed frenzy that leaves them both panting. They're too turned on to speak, but they don't need to, the most important thing is abundantly clear without needing to be spoken; they're both so turned on by the idea that it's almost blinding.  


The next time someone speaks, it's Derek, “I'd fuck them so good, Stiles.” he says, almost dreamily. And, Stiles gets it. Gets that it's the alpha part of Derek, wanting to spread his seed or some shit, but it's the human part of him, too -- wanting to explore new bodies, and relish in the fun of hooking up with different people.  


Stiles’ cock is so hard that it aches. He doesn’t think he’s ever been this hard. This is so, so, much better than the nights he spent jacking off alone.  


Derek grunts, opens his mouth to say something, and closes it again like he changed his mind.  


“Tell me,” Stiles says, hands running down his boyfriend’s sides.  


Derek shakes his head, ruts his dick against Stiles’ thigh, before shifting his weight and reaching over to the nightstand for the cherry flavored lube they keep hidden in the drawer.  


Stiles worries for a second that he’s changed his mind, thinks it’s too weird, but that thought leaves his mind quickly when he feels Derek’s cock leak a gob of precome onto his hip.  


Stiles leans up, catches Derek’s earlobe between his teeth, “C’mon, Der, tell me.”  


Derek doesn’t say anything while he fumbles for the lube, and Stiles thinks he’s really not going to, and then Derek pulls back a bit, looks him in the eyes, “I want you to lick their cum off of my cock.”  


And, had this been a few years ago, when Stiles was less experienced at holding back orgasms, he would’ve came. He’d never thought about it before, not really, too caught up in the fantasy of the during that he never really made it to the fantasy of the after but, god, he wants it too. He’s eaten a few girls out before, knows how they taste, and wants more than anything for that taste to be mixed with Derek.  


He nods quickly, too quickly, “I would, God, I would.”  


“Yeah?” Derek squirts lube onto fingers and Stiles feels the solid pressure against his hole, “Could you do that? Could you be a good boy while I fucked her? Clean up after us, afterwards?”  


Stiles nods frantically. He could, he so could, “I would. I'd lick your cum out of her, too, Derek.”  


The last word breaks into a moan as Derek pushes another finger into him. He doesn't need much prep, not really, they'd fucked last night, but Derek’s always thorough. And, who is Stiles to complain about something that feels so good?  


“No.” Derek says, pupils blown wide -- Stiles hasn't seen Derek this wrecked since the peeing incident, “That's hers. You don't get to have that cum, it's hers.”  


He punctuates by adding a third finger, and Stiles thighs jerk. He wonders how Derek could be so good at knowing all the things that push Stiles’ buttons when they've never talked about it before, but then he figures that it's Derek and he's Stiles and even if Derek doesn't know all the little things about this kink, he still knows Stiles.  


“God, Stiles.” Derek says, and Stiles can tell he's surprised. He didn't think he'd be into this, but he is. He so is.  


Stiles is nodding, grabbing at Derek’s shoulders, “Fuck me. Please, God, fuck me.”  


Derek is nodding, and the fingers pushed up in Stiles’ hole are retreating, and then Derek’s pushing at his hip, “Up. On your knees.”  


Stiles complies, flipping over, resting his forehead on his arm, and says, “Please” when Derek is taking too long. Then, he hears the little intake of breath Derek always takes right before he pushes in, and then he’s doing just that -- pushing his cock inside of Stiles, hands gripping his hips. Stiles moans and shoves his hips back, because he needs it. The feeling of Derek pushing into him never gets old; the stretch, the burn, the way it makes him feel vulnerable. And, by the way Derek is breathing and how his thrusts have already become erratic, Stiles can tell this isn’t going to last long, and that’s okay with him because, honestly, he doesn’t think he can last long anyway.  


Derek is panting when he says, “I’d fuck them just like this, in our bed. Stiles, shit.”  


Stiles keens, because he is 100 percent on board with that idea. God, he wants it so badly, “Yeah, fuck. Derek. You’ll look so good together… both of you… your cock in her cunt..”  


Stiles recognizes he’s not making much sense. It’s too far gone to do anything about it.  


“Yeah? Is that what you want?” Derek asks, picking up his pace behind Stiles, “Want to share my cock?”  


Stiles pictures it; the most intimate part of Derek’s body inside of someone else. Stiles imagines sharing him, sharing his cock -- how Stiles would be Derek’s, but Derek wouldn’t be Stiles’. Jealousy pools in his groin, and it makes it better. So much better. And, Stiles comes so hard that it almost hurts. His cock spurts come out onto their sheets, and the muscles in his thighs twitch as the muscles in his arms give out entirely. He’s not normally vocal when he comes, but this time he is -- he grunts so loud that it kind of hurts his throat.  


Derek’s pace becomes even more erratic as he leans down to cover Stiles’ back, breath hot on the back of his neck, and bites down on Stiles’ shoulder as he fucks him through his orgasm. Stiles is sore, and fucked open, when Derek finally comes inside of him.

Eventually, after several long minutes of catching their breaths, they manage to maneuver themselves up onto their pillows - cuddling together like the sappy cliche that they’d both deny they were. Stiles feels more blissed out than he can ever remember feeling, and he was so fucking glad he’d told Derek, because if he hadn’t then he wouldn’t feel this good right now.

**Notes for the Chapter:**

> I do plan on continuing this fic in the future! I'm very excited about working on a second chapter, and plan to start as soon as I can. If you liked this fic, or didn't like it, your feedback is more than welcome. Thank you for reading <3


	2. Chapter 2

**Summary for the Chapter:**

> The one with discussions, and more smut.

**Notes for the Chapter:**

> So, I wanted to take a moment and add something that I didn't add last chapter (I blame sleep deprivation).  
> This fic is purely fictional. And, it's purely fantasy. This is in no way meant to be a model of non-monogamy. Cuck-relationships can be incredibly healthy, or incredibly unhealthy. In general, in real life, they're a lot more complicated than as presented in this story in their fictionalized form.  
> I'm sure 99% of the people who read this already understood that, but just to be clear because I feel like I need to add a disclaimer. Not that anyone reads them, anyway. :p

For a while, they don’t really talk about it outside of the bedroom, or in any semi-serious context. Stiles doesn’t bring it up. He doesn’t want to force, or pressure, Derek into it, and he was hoping that Derek would be interested enough to bring it up for himself, but he doesn’t. And, Stiles tries not to be disappointed, because he understands that it’s a lot to ask of Derek -- having sex with someone isn’t a small thing, and he understands why Derek wouldn’t want to be that intimate with strangers, but it doesn’t change the fact that he wants him to. It also doesn’t change the fact that Stiles spends all of his Stiles time jacking off to the idea of it, or that almost nothing else seems to get him hard anymore. 

A few days after Stiles tells Derek, he’s home alone. Derek picked up an extra shift at work, and it’s the first time Stiles has really had the opportunity to get in some special Stiles time. He’s on their bed, hand around his cock, and he lets his mind fully go to the place he’s been trying to keep it out of. It’s different now that he’s told Derek, now that he knows Derek is turned on by the idea. The feeling of jealousy is intensified 10 fold but, god, it makes it so much better. It feels more real now. 

This time, when he closes his eyes and goes to his secret stash of fantasies, the girl is different. The curvy blonde has been replaced by a thin brunette with incredibly long, incredibly lean, legs that wrap around Derek’s waist as he pistons into her. Derek’s hair is messy in the way it always is when he has sex, and the girl’s lips are swollen, eyes heavily lidded, as she looks over at Stiles. Derek’s moaning in a way Stiles’ hasn’t ever heard before, and the little voice in the back of his mind whispers, ‘it’s because she’s better than you.’ and Stiles would be lying if he said that wasn’t a huge part of his kink. It doesn’t take long to get off on the idea, it never does, and Stiles is coming before fantasy Derek and fantasy girl do, but he stays in the fantasy even after he’s came, milky white streaks of his own cum on his abdomen. He let’s his cock go soft, and keeps picturing Derek and fantasy girl rocking together, finding a pace that’ll bring them both off. He knows that if it was real, he'd come before them -- there's no way he wouldn't, this turns him on too goddamn much, and that he'd end up sitting on the floor watching them fuck while he was completely spent. And, he lets himself think about what Derek wanted; about him crawling over to the bed that was supposed to belong to him and Derek, that Derek was cuddled up with a woman in, and gently cleaning her cum off of his oversensitive cock. The jealousy is more intense without the arousal to take the edge off but, fuck, it’s good -- this feeling. Picturing his boyfriend be so fucking good for someone else, like a man should be, and the shame and humiliation that came along with it, with the idea that he wasn’t enough, was this perfect combination that made jealousy and arousal become an entangled thing. He couldn’t seem to have one without the other, anymore.

He's nervous when Derek gets home. He’s decided to bring it up again -- about doing it seriously. It's something he's not even positive he wants, there's people online who say they loved the fantasy but hated the reality, but he honestly can't imagine not trying.  
He makes one of Derek’s favorite dinners, because he can, and afterwards they end up curled up on the couch. Stiles is going through the little speech he prepared one more time. He's tracing circles in Derek’s arm when Derek goes, 

“What, Stiles?” 

“What, what?” Stiles says, blinking.

“I can hear you thinking.” 

Stiles huffs, “that's not a thing.” 

Derek glares, but there's no heat to it. 

“I was thinking about that, um,” his cheeks are getting hot, “thing we talked about the other day.” 

“Oh.” Derek says, nods, and Stiles curses him for being the world's worst conversationalist. 

“Obviously, it's not my decision, because, like, it's your body, duh, obviously.” Stiles takes a deep breath, begging the powers that be to stop him from rambling, “but, I was wondering if, maybe, you'd like to actually pursue it.” 

Derek's quiet for a moment, and that's really not unusual, because he's Derek and he's always quiet, but Stiles is tense and it feels like a lifetime before he says, 

“Are you sure that's something you want?” 

Stiles heart almost stops beating, because that's not a ‘no’, and he's nodding his head before he can stop himself, “Yes, yes. I do.”

“Once we do it, Stiles, there's no going back.” Derek says, and he's so serious, “I can't un-sleep with someone.” 

“I know.” Stiles says, “I've thought about this a lot.” 

“I have too.” Derek admits, and Stiles’ eyes widen, “After, y’know, we talked about it, I couldn't get it out of my head.” 

Stiles could feel himself getting hard, and he willed himself to stop, because this was not the time. This was srs bsns.

“I want it, too, Stiles. I've never thought about fucking someone else since we’ve been together but, now, it's like I can't think about anything else.” Derek says, voice tight, “I feel so shitty about it, like I'm betraying you. And,” 

Stiles is shaking his head, cutting him off, “No, no. I want this, too.” 

“I know you do, I know, but I'm afraid I'm going to say or do something wrong and hurt you.” Derek says, and he's so earnest in it that Stiles kisses him. He knows his Derek would never hurt him. He's such a good man, and Stiles would be selfish to keep him all to himself. 

“Der, you're not going to hurt me. This is a turn on for me, probably my biggest turn on if we’re being honest.” he says, “I want you to want this. I want you to get off on it, too.” 

“I just,” Derek sighs, and Stiles can see him trying to work out how to word what he wants to say, “I could never share you, and because of that, I don't understand how me saying I want to fuck other people doesn't hurt you.” 

Stiles smiles a little because, God, his boyfriend is sweet. He wants to be closer to Derek, and the only way he can think of to get there is to be in his lap so he moves, motions for Derek to move his hands, and straddles his hips. His hands rest on Derek’s sides, and Derek hands end up on his hips. There's a little smile on Derek's face, too, and Stiles figures Derek was craving the closeness, too.

“I don't understand it, either, but it makes me so fucking horny to think about it, and hearing you talk about it is so much better. And, honestly, yeah, I do get jealous, but that turns me on, too. It's like, the more jealous I am, the more turned on I am.” Stiles confesses, prays Derek doesn't think he's a freak, and continues talking, “it's hard to explain because I don't even really understand it myself.” 

Derek nods, and says lowly, “Maybe it's the alpha in me, but I love the idea of you sitting at home, being just for me, and me being out -- hooking up with girls.” 

Stiles psychically twitches. He's so fucking turned on, and Stiles doesn't understand how they're here, how they're both on board with this, but they are. 

“It's been so long, Stiles.” Derek says, drops his head to his shoulder, “it's been so long since I've been with a woman.” 

Stiles’ cheeks flush again, “You crave it, don't you?”

Derek nods against his shoulder, grips Stiles’ hips like it's physically hurting him, and Stiles exhales shakily. Because this is what he wanted, for Derek to crave things that Stiles couldn't give him. It makes his heart ache, but it makes his dick ache, too, and Stiles realizes how intense it’s going to be when this actually happens. When, he realizes, when. Not if. 

He jerks his head up, a little unexpectedly as it hits him, “We’re really going to do this?” 

“Yeah, Stiles, we are.” Derek says, and his hands slide from Stiles’ hips to his ass.

Stiles groans as the wave of jealousy and arousal slam into him, and he realizes it’s ridiculous. Dereks not even touching him, not really, but he can’t help it. He needs to get off, he needs to come, “Derek -- bedroom.” 

And, Derek, thank fucking God, actually obeys for once. He’s picking Stiles up, and Stiles has never been more grateful for werewolf strength in his life. He keeps repeating, ‘this is real’ over and over in his head, because his biggest fantasy is going to come true. Dereks actually going to do this for him. Derek wants to do this. 

Then, he’s on the bed, looking up at his greek god of a boyfriend, and whispers, “Fuck, Derek.”

Derek pulls his own shirt off, and then kneels over Stiles, a leg on each side of his hips. His pupils are so dilated that Stiles can barely see the blue green of his eyes anymore. Derek says, “I’m gonna fuck you so hard.”

Stiles groans as he starts working on Derek’s belt because, yes, please. He is here for that. 

Then, Derek is leaning down, biting onto Stiles’ earlobe before whispering, “Stiles, do you remember a few months ago?”  


Stiles’ brows furrow together, “Be more specific, Der.”

“When I didn’t let you come for a week.” Derek says, “Do you remember?” 

Oh, does Stiles remember. That’d been when he and Derek really got into power play. Derek had pushed all of Stiles’ kink buttons that week, and wouldn’t let him come. It was frustrating, and maddening, but when he’d finally been allowed release it was insanely good -- probably one of the best orgasms of his life. 

“Of course.” Stiles says, and maybe if he wasn’t brain dead from lust, he’d would’ve caught on where Derek was heading with this. 

“I don’t want you to come.” Derek says, “I don’t want you to come until after I’ve fucked someone else.”

Stiles squeezes his eyes shut, because fucking hell that’s another one of his fantasies, and he wonders if werewolves have suddenly developed the ability to read minds and no one filled Stiles in. Sounds like something they’d do. 

“I don’t know if I can.” Stiles whines, honestly, because he’s been coming 3 or 4 times a day -- every time he thinks about this, and he doesn’t know if he can go until Derek finds someone. Not that it’ll take him long because, hello, he’s Derek. 

“You can, you can.” Derek says, kissing down his neck, “You can be a good boy for me.”

Stiles’ hips jerk, and he brings his hands up to grab at Derek’s lower back.

“You can keep your little cock in your pants while I go out and use mine, can’t you?” 

He nods, he nods frantically, because that’s the hottest thing that’s ever come out of Derek’s mouth. And, he can -- he can do that for Derek. He’ll wait, it might just kill him, but he’ll do it. 

Derek, the bastard, decides that this means that he can take his time with Stiles; he can spend as long as wants sucking hickies into his skin, opening his jeans with his fucking teeth, and mouthing at Stiles’ cock through his underwear. Luckily for Stiles, the week he’d been forbidden to come, had given him a lot of practice at holding orgasms back, because if it hadn’t of he probably would’ve been getting close. Damn Derek, and his mouth. 

Derek bites onto the elastic of Stiles’ underwear, and lets them snap back against his skin. Stiles pushes at his head, and mumbles, ‘ass’ under his breath. Derek kisses Stiles’ hip bone, and makes eye contact, 

“Der, c’mon.” Stiles pants, gives Derek his best puppy eyes, because if he doesn’t -- Dereks going to absolutely kill him before this is over, “I need you to fuck me.” 

And, that gets him. Like Stiles knew it would. He wonders if Derek’s future fuckbuddies will figure that trick out, too. He bets they will. Those girls are going to be so lucky to have him. 

Derek backs off the bed so he can get his own jeans and underwear down, as Stiles shimmies out of own pair, damp with Derek’s saliva, and his own precome. Derek spreads lube onto his fingers while he's up, and Stiles takes the opportunity to just look at him. When they're fooling around, Derek is a very tactile person, so Stiles doesn't get to just admire Derek very often, and when it does it always almost takes his breath away. Derek is beautiful; pale skin stretching over the perfect amount of muscle, dark hair in beautiful contrast to that gorgeous skin, and, his cock, god, Stiles has always loved his cock. Long without being too long, thick without being intimidating. Stiles remembers that he has to share that now, and a shiver runs down his spine. 

Stiles is opening his legs before he can stop himself, because even if he can't cum, he still needs Derek inside -- he feels too empty without him, “Der.” 

Derek growls, actually growls, as he climbs back on top of Stiles. He leans in close to Stiles’ ear as he's pushing his hand down to Stiles’ hole, and says, “I bet she'll be tight, tight like you.” 

Stiles pushes his head back, bares his throat, and keens. 

“Tighter, even.” Derek says, a hint of uncertainty at going too far that is quickly washed away by Stiles’ enthusiastic reaction. 

“She's gonna feel so good, Stiles. Nice and wet for me.” Derek says, pushing two fingers inside of his boyfriend, and grunts, “I haven't had someone get wet for me in so long, Stiles.” 

Stiles’ thighs jerk and, god, it's hot; being reminded of all the things they'll give Derek that he just can't, “Der, please. I need it.” 

He must sound desperate, because it prompts a response from Derek as he pushes in a third finger, “No. Don't come, Stiles.”

Stiles shakes his head, because no, no, that's not what he means.

“What, baby?” Derek's mouthing at his thigh between words, “You need me to fuck you? I'm gonna, Stiles, I'm gonna fuck you so good.”  


Stiles shakes his head again, because it's not that either. He gasps, and then rasps out, “I don't need to come, I don't need you to fuck me. I need you to fuck her.”  


It pulls a groan from Derek, and he drops his head down, bites at Stiles thigh. And, Stiles realizes it's true. He gets it, now. He gets why jacking off, being fucked, even, only takes the edge off for a few minutes -- it's because it's not what he needs. Stiles knows, now, that he's not going to have relief until Derek’s cock is deep inside of someone else. It makes his own cock twitch.

When Derek tears himself away from his thigh and looks back up at him, it's with alpha eyes. Stiles’ eyes widen slightly, because that's only happened once; the time Derek peed on him. And, Stiles realizes that just how much this must be appealing to Derek’s wolf. He's finally going to have a female mate, someone who's little cunt will clench around his cock, and who can give the wolf cubs. Stiles reaches down, grabs Derek by his face, and guides him up toward himself. 

They're kissing before Derek squeezes his eyes shut, and when he opens them, they're human again. 

“I want to ride you,” Stiles says, because he knows it's Derek's favorite. If this is the last time that Stiles has Derek’s cock before he has to share, he's gonna make it good for him. His arousal level rises further at the realization that he's trying to impress him, that he now has to be better than other people at taking Derek's cock. 

Derek nods, quickly, because he loves it when Stiles rides him and rolls them over. They spend a few moments moving the pillows around, and getting comfortable. Stiles picks up the bottle of lube, squirts some into his hand, and then spreads it down Derek's cock. He can feel his hole gaped open slightly, desperately wanting to be filled. He scootches up, then, straddles Derek's hips, and reaches behind him for Derek's cock so he can guide it inside, and he's reminded again that Derek's cock isn't going to be his for much longer, maybe it already isn't. That some girl, maybe multiple girls, will be doing this exact same thing for him soon. He moans as he starts to sink down onto Derek's cock. Derek's hands come up to grab his hips, and Stiles throws his head back. It feels so good to have Derek in him, his hole welcoming the intrusion like it has hundreds of times before.

Derek groans quietly, “You look so fucking good like this.” 

Stiles sinks further down, and moans, as he brings his hands forward to rest on Derek's chest for leverage.

Stiles can tell that Derek's extremely turned on, maybe even more so than last time, and so it doesn't really surprise him when Derek bucks his hips up. He grunts, and shifts his weight, before sliding all the way down Derek's cock. His breathing is heavy, because taking Derek like this is always so much more intense. 

“Tell me,” Stiles says as he starts to push himself up slightly, inching up Derek's cock, and he'll probably regret it since he's not allowed to come, but he's too turned on to stop himself, “tell me what you want to do to them, what you want me to do while you fuck them. Der, please.” 

“You're gonna be a good boy for me, then, too Stiles. You're not gonna touch yourself, you're not gonna cum until she's gone and I'm fucking you.” Derek says, but it's labored, pushed out between groans. 

Stiles whines, thighs shaking as he rides him, “I don't know if I can.” 

“You will, unng…” Derek says, “I'll tie your hands behind your back if I have to.” 

Stiles wants that, God, he wants that so bad; to be bound up as he watches them fuck. 

“What if I come without touching my cock?” Stiles groans out, because it's a legitimate possibility. He's never done it before, but if anything can bring him there -- it's this. 

Derek pushes his head against the pillow, hips thrusting in times with Stiles, “that's the only way you're allowed to come, if it's before I tell you to.” 

Because, fuck, if Derek can deny something that hot. 

Stiles starts to lose his rhythm, too turned on to keep the pace. His hole is spasming around Derek's cock like he’s coming, but he's not; he wouldn't do that, he wouldn't disobey Derek. So, Derek rolls them over, hiking one of Stiles legs over those muscular shoulders and driving in. They're so close, Stiles can feel his breath on his face, and he trembles because she'll get to have this, too; the beautiful look Derek gets on his face as he's about to come. 

And, when Derek does come, he comes hard. He pushes so deep into Stiles that it almost hurts, but it’s good, too.

 

They cuddle up, like always; Derek the big spoon to Stiles’ little spoon. Stiles is still hard, because he was a good boy, and didn’t come. And, Derek’s running his hand across Stiles’ hip. Derek is warm, like a furnace, thanks to his wolfy side and Stiles loves it -- except during the California summer. Derek’s beard is scratchy at the back of his neck, but it’s good. It’s Derek. 

Usually, it’s Stiles who breaks the silence, or gets up first, because he’s Stiles, and he never quite got the hang of being still. This time, though, it’s Derek, “Stay here, I’ll be right back.”

Stiles watches him go -- beautifully sculpted ass slowly leaving his view. Once he’s gone, Stiles stretches out; reaches his arms up above his head, and points his toes. He may not have came, but he still has the post-sex fucked out feeling that he loves so much. 

When Derek comes back, it’s not with the glass of water Stiles is expecting. Instead, he has his phone in his hand. Stiles squints, because that’s not normal Derek behavior. Dereks never been the ‘stuck to his phone’ type. 

Derek seems to sense his confusion and says, “Want to help me figure out how to work dating apps?” 

Stiles’ cock, that was slowly starting to go soft, quickly starts to harden again, because, yes, yes, he did. 

They decided on Tinder, first, because it was free and there were probably a decent amount of girls who were just there for hookups. They connect Derek’s facebook, and Stiles hopes that no one who knows them finds Derek’s profile, because this isn’t something that he feels like talking about with other people. Stiles makes Derek put up at least one of his shirtless pictures, because, c’mon, if Stiles looked like Derek then he’d just stop owning shirts. Derek, of course, insists on having the other pictures be ‘respectable’, because,  
“Stiles, I’m not a stripper!” 

Derek included in his bio that he had an open relationship with his partner. They figured anything else beyond that, like the fact Stiles wanted to watch, could be left for private conversation. 

And, then, came the swiping. Stiles leaned his head on Derek’s shoulder and watched as he swiped right, or left, depending on his preference. Stiles’ cock was throbbing, and the jealousy he felt was more intense than it had ever been. He was suddenly grateful that Derek hadn’t let him come, because he didn’t know if he’d want to feel this jealous without being aroused, too.

**Notes for the Chapter:**

> I wanted to thank everyone for their amazing feedback, because it has seriously made my week. Sometimes, with this kink, you can end up feeling quite alone because it's not a kink anyone ever talks about, and I just wanted to express my gratitude for everyone who commented about sharing this kink with me. You're freaking fantastic. 
> 
> Also, chapter 2 was originally intended to be "the" chapter, but then it just kind of morphed into this. I'm planning for next chapter to be "the" chapter, and this time I'm pretty sure it will be. 
> 
> LAST THING I SWEAR, I've gotten really, really, into this fic and there are a lot of different scenarios that I'd like to explore with it. However, there's no way that I can do that all in one chapter (unless the chapter was 10,000+ words long, and I'd rather keep all the chapters roughly the same length :p), so the question is; if I wrote more than 3 chapters, would you be interested in them?


	3. Chapter 3

**Notes for the Chapter:**

> This chapter was a lot to write, and I have a feeling it'll be a lot to read. 
> 
> I must warn that there is an emotional scene following a cuckolding situation, and it's quite intense. If you're uncomfortable with crying after sex, because of sex, then you may want to proceed with caution, or stop reading. You've been warned.

It’s kind of weird. There’s a constant undercurrent of excitement, and arousal, and anxiety. There were moments when Stiles almost had to sit on his hands to stop himself from jacking off, and other moments when the anxiety became almost too much and he considered calling the whole thing off. Stiles wasn’t stupid. Derek was a wonderful man, and Stiles was sure that there were plenty of wonderful women out there, and he would be crazy if he didn’t at least think about the possibility of Derek getting emotionally attached to one of them. But, he knew Derek. He knew Derek loved him, wanted him more than anyone else, and he still craved watching Derek be with other people more than anything, so he didn’t call it off.  
He and Derek did talk about it, though. They talked a lot about everything. Derek made sure Stiles knew that he had veto power -- that if he didn’t like something, or someone, he could say no and Derek would listen. No questions asked. 

They set boundaries; Derek has to tell Stiles everything -- no secrets, either one can back out at any point, and, for now, Derek can’t fuck the same girl more than once. There were others too, like how they can’t spend the night, or touch Stiles - Derek’s boundary, can’t you tell? - but those were the main ones. They made Stiles feel better in his anxiety laden moments, like he was still in control. 

Just because Stiles has anxieties about what they’re doing doesn’t mean he isn’t still turned on by it, because he is. He’s in an almost constant state of arousal, and he still hasn’t had any relief, because Derek is a dick. He has become almost obsessed with the idea, and felt like he psychically needed it at this point.

Sometimes the jealousy, and therefore the arousal, would spike to a point that it almost became painful. Derek had started messaging back and forth with several women online, and Stiles became aroused everytime Derek’s phone lit up with soandso ‘sent you a message!’. Sometimes Stiles would lean his head on Derek’s shoulder and read the conversations, and other times he wouldn’t -- just let his imagination run wild. There was one girl in particular that Derek had been messaging with, who was really into the idea of Stiles watching, that looked promising. Stiles noticed how Derek got a smile on his face everytime he got a message from her. It made that sickening combination spread through his veins like wildfire. 

 

It’s almost 4 days after they officially decided to go through with it, when Stiles is sitting up in bed reading a book, that Derek sits on the edge of the bed with his serious face on. He’s only wearing a towel, hair wet from the shower. 

“I have a date tomorrow night.” He says  
Stiles heart stops beating. His cock goes from being completely uninterested to fully interested so fast that it’s almost dizzying. Stiles nods, “Okay.”

“She wants to go on a date first, get to know each other a bit, see if we have chemistry.” Derek says, “If that goes well, she’ll come over sometime this week to hook up.” 

“Okay, okay.” This is real. This isn’t fantasy. Derek actually has a date with someone else, 

“What’s her name?” 

“Samara.” Derek says, and Stiles knows she’s the one who Derek likes the most.

Then, Derek’s standing up, dropping his towel, and climbing on top of him. Stiles’ book ends up on the floor as they start kissing. Derek’s hard, too, pressed up against Stiles’ thigh, and Stiles groans. Derek pulls back and says, 

“I want you to help me get ready tomorrow.” He starts kissing down Stiles’ neck, “Can you do that for me? Get me ready for Samara?” 

Stiles nods, frantically, because he can. He wants to. And, it’s better now. The jealousy that Stiles gets off on so much is in full swing, and his hips, covered by his pajama pants, push up into Derek’s. She’s real, she has a name, and Derek’s going on a date with her, and it’s the hottest thing in the world. 

“Derek, fuck.” Stiles’ face is flushed, “Fuck me, fuck me.”

Derek shakes his head, kisses Stiles and says, “Not until after.” 

Stiles groans. This was one of the things they talked about, Derek knew how much it would turn him on, and he did it for him. He’s grabbing onto Derek’s upper arms, and tucking his face into his neck, because this is just too much -- he wonders vaguely, in the back of his mind, whether or not you can die from being too aroused. 

Derek, the bastard, kisses him and then rolls off onto his side of the bed. He stretches his arm out, and pulls Stiles in. He then reaches down for the blankets so he’s not as exposed. 

“Der?” Stiles says.

“Hmm?”

“Thank you.” And, Stiles gets that it’s weird. He’s thanking his boyfriend for fucking other people, but he feels like he needs to. Derek would never have done any of this on his own. 

“No,” Derek shakes his head, “Thank you. You’re so good, Stiles.”

Stiles starts to shake his head, because he’s not. He’s asked Derek for so much -- way more than Derek has ever asked him for. 

“You are, Stiles, you are.” Derek says, tilts his face down to kiss him, “You’re such a good little cuck.” 

Stiles feels his hips twitch; that fucking word gets him every time it comes out of Derek’s mouth. 

 

The next day, Stiles is a bundle of nervous anticipation. He can barely focus in his math class, and he almost walks out in front of a car on his way back to the parking lot. He’s so fucking excited for tonight that he doesn’t know what to do with himself once he is back home.  
So, he cleans the living room. And, then, the bedroom. And, then, the bathroom. Waiting for Derek to get home from work is torture. He knows that the waiting tonight will be even worse so he tries to calm himself down. 

Derek gets home at 5. He makes sure to kiss Stiles, ask him if he’s still sure he wants this, and then goes to take a shower. He takes longer than usual, and while he’s in the shower his phone lights up with a notification from Samara. Stiles forces himself not to read it, and goes and lays out Derek’s clothes instead. 

They’re going to a nice restaurant, and Derek should probably wear a tie. Stiles gets that it’s weird. He does. He happily picking out his boyfriends clothes to wear on a date with a, presumably, beautiful woman. Just because he understands that it’s weird doesn’t stop his cock from getting hard. 

When Derek gets out of the shower, he wraps his arms around Stiles’ waist, and kisses the back of his neck, and asks him for the 100th time, “Are you sure?”

Stiles nods, and he’s telling the truth. Each passing second makes him want it more. 

Derek puts on his nice suit. He looks so calm, but Stiles can tell he’s excited too. He’s been looking forward to this probably almost as much as Stiles has. 

 

Derek kisses him again before he leaves. He looks good. Stiles has never been the fancy dinner type, so sometimes he forgets how great Derek looks in a suit.  
When Stiles is alone, he tries to focus on things other than the jealousy pooling in his gut. He tries to read, tries to fix himself some dinner, tries to watch a movie, tries to do anything but think about what Derek’s doing, but it doesn’t work. 

This is real. This isn’t a fantasy, anymore. Derek’s really out on a date right now, while Stiles sits at home and waits for him. ‘Like a good little cuck’, his brain supplies. Stiles’ mind keeps wandering to what Samara looks like. He’s never seen her as Derek swiped on her while he was out of the house. He wonders how much cleavage she’s showing Derek, how short her dress is, if Derek will slide a hand up her skirt at the end of the night -- if she’d let him. 

Stiles is hard, cock tenting his pants, and he can’t wait for Derek to get home. He can’t wait for Derek to tell him all about it. 

The date creeps into the third hour, and Stiles knows it has to be going well, and, by default, he’ll be sharing Derek soon. Well, he’s already sharing Derek, but sharing the more intimate parts of him. 

Derek comes home late, and Stiles is waiting up. Of course he’s waiting up. There’s no way he could sleep. When Derek comes through the door, Stiles stands up from his seated position on the couch. He’s still in his suit, and looks pretty much the same, except for the smear of red lipstick on his mouth. Stiles’ cock leaks. 

“Did you kiss her?”

Derek nods, and looks concerned. Like, maybe he thinks Stiles is regretting this, “Are you okay?”

Stiles practically pounces on him, and he’s once again grateful for werewolf strength. This close, Stiles can smell her perfume. He can feel Derek’s erection, and he wonders who that’s for; him, or Samara? 

Stiles is nodding, “Tell me everything.”

“Fuck,” Derek breathes out, and then they’re kissing. Stiles waits for the hint of someone else’s taste in Derek’s mouth, and is slightly disappointed when it doesn’t come. Derek’s walking them towards the couch, the bedrooms just too goddamn far, and Stiles is pawing at his chest, his back, his shoulders -- wondering which of these parts that she touched, too. 

He’s laid out on the couch, legs open, with Derek fit snugly in between. He pleads, “Derek, Derek.”

“She’s so beautiful, Stiles.” Derek says against his cheek. 

Stiles’ legs tighten around Derek’s hips, and he grinds upwards. He feels like he’s a 15 year old boy, about to come in his pants. 

“She was so flirty, too.” Derek says, as he leans up to take his own suit jacket and shirt off.

“Did she touch you?” 

Derek’s nodding as he lays back down over him, “She’s so tactile, Stiles. She kept touching my arms, my back, my thigh.” 

Derek puts emphasis on the last word, and Stiles groans. He starts pulling at Derek’s belt, he needs him. 

“I want you to suck me off, will you do that?” Derek asks, and Stiles nods. He will, he absolutely will. 

They shift around until Derek is sat on the couch, and Stiles is kneeling between his spread legs. Stiles thinks this is probably for the best, because he doesn’t think he could’ve held back an orgasm while Derek fucked him. Stiles’ cock is somehow even harder than Derek’s. He’s spitting on it to get it wet enough, and then wrapping his fingers around the girth. Derek’s got his hands in Stiles’ hair as Stiles starts to take him into his mouth. This isn’t something they do all the time, but Derek’s familiar enough, and the taste isn’t so bad so Stiles always finds that he enjoys himself. Or, at least, enjoys the reaction it gets him, and the sounds Derek makes.

“Fuck, fuck, fuck” Derek’s repeating, not making any sense, until he says, “I took her home, and walked her to her apartment, and, fuck, I kissed her.”

Stiles has to reach down between his own legs to squeeze his cock to stop himself from coming. 

“She put her tongue in my mouth, Stiles, shit, shit,” He’s breathing heavily as Stiles presses his tongue flat against the underside of his penis, “and she pushed up against me and, fuck, her breats…” 

Derek doesn’t finish his sentence, but Stiles doesn’t need him to. He understands all on his own. 

“I got so hard, Stiles.” He confesses, and Stiles groans around his cock, because, fuck, this is exactly what he wanted. He wanted him to want her, and he does -- he wants her so badly. It makes jealousy stab into him like a knife, but it’s good. The real thing is so much better than fantasy.

Derek is worked up enough that even Stiles’ lack of experience in giving blow jobs doesn’t stop him from coming within a few minutes of being in his mouth. 

Derek is pulling him up into his lap, still panting, as he says, “She’s coming over tomorrow.” 

 

If Stiles thought that the day before had been anxiety inducing, this one put that one to shame. He was bouncing his leg up and down, cracking his fingers, grinding his teeth -- every anxious habit he had was out in full force. Half of it was excitement, half of it was nerves.  
The night he’d been waiting over 6 months for was finally here, and there was no going back. And, Stiles, despite his fears, didn’t want to. The way he felt last night was still fresh in his mind, and he couldn’t imagine not feeling that again. 

 

The plan was fairly simple. It was a plan that he and Derek had come up with several days prior, and amended to fit Samara’s preferences. Samara and Derek would go out on another date, Stiles would wait at home, they’d come back to the apartment after their date, they would have sex in Stiles and Derek’s bedroom with Stiles in the room, and after they finished, Stiles would leave the room to give them some alone time. After Samara left, Stiles and Derek would have alone time. It was something they were all comfortable with, and Stiles was eager. 

Derek left for his date at 6; once again kissing Stiles before he left, and asking if he was sure. He was. 

 

The first thirty minutes after Derek left was easy. Stiles had walked to his and Derek’s bathroom. He’d gotten into his and Derek’s ‘toy’ box that they kept in the bathroom closet, and pulled out the navy blue plug that Derek had instructed him to use. They’d talked about it the night before, and Derek had told him that he wanted him to be ready for after he and Samara were done.  
He spreads lube onto his fingers, and puts one foot on the lid of the toilet - classy, he knows - before reaching his hand back behind himself. He rubs the tip of his index fingers around his rim before pushing it inside. Stiles has never really gotten off on fingering himself -- can’t quite get the angle right, or get deep enough, and it often just leads to frustration more than anything else, so he makes fairly quick work of opening himself up while still making sure that he’s stretched enough. He gets the lube, and the plug, and starts the process of pushing it inside while wishing that he’d had Derek do it before he left.

After, when he’s done, he takes takes a picture in their mirror; the over the shoulder kind with just a hint of the plug showing between his cheeks. He sends it to Derek, and his cock grows to half mast when he pictures Derek on a date with a pretty girl, opening a nude from him. 

Stiles spent the next hour pacing nervously around the apartment. He’d straightened up, again, because he wanted the apartment to look nice for her. He changed his and Derek’s sheets, and made their bed that hadn’t been made in months. He was nervous and excited and he was really fucking glad that they’d decided to go through with this. 

 

Eventually, Stiles felt like it was 600 years later, they got home. He saw Derek’s black car pull up in front of their living room window, and he stood up. His hands were sweaty, and he wiped them on the front of his khakis. His stomach was twisted into a knot. His cock was, humiliatingly, already starting to harden in his pants. 

She really is beautiful, Stiles notices as she and Derek walks through the door. She has dark skin, long legs, and curly, shoulder length, hair. They’re holding hands, and Stiles’ stomach flips over. 

Derek’s mouth is smudged a deep maroon color this time, matching the color of Samara’s lipstick, as he introduces them, “Samara, this is Stiles. Stiles, Samara.” 

He doesn’t really know what to do in this situation. What do you say to the woman who’s 10 minutes away from fucking your boyfriend right in front of you? Life hadn’t prepared him for this particular interaction so he just, sort of, stuck his hand out for a handshake.

She smiles, this gorgeous smile, and takes his hand firmly, and laughs out, “Hello.”

Derek, thank god for Derek, smiles, and motions towards their bedroom door, “Shall we?” 

Stiles nods, and Samara does, too, and then they’re walking to the bedroom arm in arm. Stiles follows a few steps behind, jealousy and arousal already burning through his veins. 

Once they’re in the room, Derek turns to him. Derek cups his face, and he asks him so sweetly that it makes Stiles’ heart ache, “Are you sure?” 

Stiles knows that he can say no. That if he said ‘no’, Derek would drive Samara home and come back to him. They’d go back to normal, like none of this had ever happened. He doesn’t have to share him. He says, “Yes.” 

“Alright,” Derek kisses his forehead, “go sit over there.” 

Stiles obeys, and sits on the accent chair in the corner of their room. By the time he’s seated, Derek’s full attention is back on Samara. He’s got his big, strong, hands on her hips, and she has her hands on his shoulders. He can see that Derek’s hesitating, not because he isn’t into it, but because he’s afraid of hurting Stiles. He worries for a second that Derek is going to back out, but then Samara is kissing him, mouths fitting together in a way that is obviously practiced. Derek’s pulling her in closer, hands finding the small of her back, as her much smaller hands move up to cup his face. Stiles takes a deep breath because, fuck, that’s even hotter than he imagined it would be. 

Neither of them seem to be in a rush; they’re just enjoying each other’s bodies. Derek’s hands are all over her; her sides, her back, her hips, her ass. And, her hands are all over him; his chest, his sides, and then she’s reaching down and touching him through his dress pants and he’s groaning in pleasure from someone else’s touch, and Stiles feels it in his bones. Stiles grips the seat of his chair. 

Samara starts pushing his suit jacket off of his shoulders, and Derek’s working on his own tie, and Stiles feels jealousy stab into his gut again, because, god, oh god, this is real. It’s more intense than he thought it would be, already, and not much has even happened yet. It’s better, too. It’s even better when Derek’s shirt comes off, and she’s touching his skin. Derek’s got goosebumps rising on his back, probably from her nails, and he’s into it. Stiles knows what Derek looks like when he’s turned on, and he’s definitely turned on. 

Derek has her turn around, she moves her hair out of the way, and Derek starts to slowly pull down the zipper of her dress. When it falls to the floor, Stiles is shocked by how fucking amazing her body is; she’s lean, but she has boobs, and an ass. She’s exactly the type of girl that he’d expect Derek to be with -- perfect. 

She’s in a matching bra and panty set made of red lace, and Derek’s hands are running all over her body. She undoes his belt, and then his slacks, and then they’re on the floor as well. Derek backs her up until her knees hit the edge of the bed, and she falls backwards. She’s on her back, and Derek’s above her, and Stiles knows the hungry look he must be giving her because she makes a soft, breathy, sound, and then she’s pulling him by his forearms until he’s on top of her.

It’s so fucking hot. Derek kisses down her neck, and she’s making these noises that are practically mewls, and Stiles gets it -- he knows exactly how it feels; how attentive Derek is, and the stark contrast of the softness of his mouth and the roughness of his beard. She gets one of her legs between Derek’s, and then Derek’s hips are grinding down, and he groans. Stiles’ cock pulses in his pants that are now uncomfortably tight. 

Derek’s hands make quick work of her bra, clearly experienced from a life before Stiles, and he seems almost fascinated by her breasts. He spends time alternating from one side to the other, and Stiles can’t see exactly what he’s doing, but he knows from the pleasured look on Samara’s face, and the noises that he’s making that he must be really fucking good at it. She has her eyes closed for a while, but when she opens them, she looks directly at Stiles; they’re a deep brown, far darker than his own, and filled with lust. He knows that she’s as turned on as he is. 

Derek gets them both worked up enough that their underwear comes off quickly. His cock has turned a deep shade of purple from how hard is, but he still doesn’t rush into fucking her. He has her spread his legs, and then settles in between them. He noses at the dark curls there, and Stiles knows the second he actually starts to eat her out by the way Samara throws her head back and lets out a groan. 

He spends, what seems like an eternity, between her thighs. And, fuck, does she love it. She’s gripping her own thighs, then the bed covers, and then threading her fingers through Derek’s hair. Stiles can see Derek’s cock spurt out a drop of precome as she says, “Derek, please. Fuck, Derek, please.” 

She sounds desperate for it, for Derek, for his cock, and he gives in. He’s moving back up her body, trailing kisses along the way, and kissing her on the mouth. Stiles can see his tongue slide into her mouth, and she knows she must be tasting herself -- knows that he’ll be tasting her on Derek’s tongue later. 

Finally, finally, she’s reaching down between her and Derek’s bodies, grabbing his penis and giving him a firm stroke. Stiles feels his jealousy spike, because that’s Derek’s fucking cock she’s touching -- one of the most intimate parts of Derek’s body, a part that’s always been Stiles’, and now it’s not, anymore. Then, Samara is guiding it forward, and Derek is thrusting his hips, and then he’s inside of her. And, there really is no going back. She’s got one of her legs around Derek’s hip, and Stiles can see where he disappears into her, and it’s like a punch to the gut. 

Derek lets out this sigh of relief when he’s all the way, his pelvis pressed up into hers, and she’s digging her nails into his back already. He watches, waits for the marks to disappear, but they don’t, because Derek isn’t letting them -- he wants them there, wants her marks on his skin. Stiles bites into his palm to stop himself from making noise. 

The pace they set is almost brutal, so different from the leisurely kissing that they started with. Derek is fucking into her, and she’s moving her hips with him, and Stiles knows it must be so fucking good for them both. They look beautiful, too; Derek’s hair sticking to his forehead, her beautiful long legs wrapped around his body, the way their skin contrasts -- they’re just really fucking beautiful together. 

Derek starts coming undone faster than he usually does; Stiles doesn’t know if it’s the situation, or because he’s missed women, or if it’s Samara in particular, but he’s quickly losing his rhythm. He’s loud, too, louder than he usually is. And, she’s into it, too. She’s got his hands all over him, and she’s moaning, and every once in awhile, when Derek hits a particularly good spot, she moans out his name.

He glances over at Stiles, who is gripping his own thighs and flushed in the face, and Stiles can see the pure ecstasy on his face. It makes Stiles’ cock start to throb painfully, his asshole clenching down on the plug placed snugly inside -- aching to be filled by Derek’s cock.The jealousy and arousal is building in him like a crescendo, and he’s panting. 

Then, suddenly, Derek pushing in as deep as he can, and coming, moaning out, “Samara, fuck.” 

She’s coming, then, thighs clamping down onto Derek’s hips, back arching, and moaning out his name, too. 

And Stiles, is breathing heavily, more turned on than he has been in his entire life, and, frankly, really impressed with himself for managing not to come untouched.

 

Derek’s breathing heavily as he rolls off of Samara, who moves up further onto the bed -- laying back on Stiles’ pillow. Derek, however, moved to the edge of the bed, and spreads his thighs, and says to Stiles, “C’mere.”

They talked about this. About what Stiles was supposed to do after, but nothing could’ve prepared him for just how humiliating it would be, or how hot it would be. He slunk to the floor, and crawled on all fours over to kneel between Derek’s spread legs. Derek ran his fingers through his hair as Stiles took a deep breath, and leaned forward. It was just Derek’s cock, but it wasn’t. It was red from sex, and covered in white fluid that was definitely not semen, and definitely not Derek’s. He opened his mouth, and took the tip of Derek’s cock into his mouth as Derek made a hissing sound from overstimulation. It didn’t taste like Derek, instead it tasted a mix of Derek and his lover, and Stiles couldn’t get enough. He alternated between sucking, and licking, to get every drop off of Derek’s cock. As he was licking around the base of his cock, where her cum was the thickest, the reality of everything smashed into him. Derek had fucked someone else -- the cock that was in his mouth had been inside someone else just a few moments before, and then Stiles is coming. He didn’t even touch himself, but he’s coming, and it’s the most intense orgasm of his entire life. His entire body convulsing, hole clenching tightly around the plug, and his cock releasing so much cum that there would be a visible wet spot through his pants. 

“Holy shit,” he heard Samara say, “did he just come?” 

He didn’t hear Derek say anything, just stroke his hair patiently while Stiles came down from his high. When he did come to, Derek was looking at him with the look that resembled something akin to awe, but he didn’t say anything about it, instead, he took a deep breath and said, “Finish.”

He motioned to his cock, and Stiles went back to licking the last of her come off of the base. The humiliation, and jealousy, were intensified post orgasm. His cheeks were flushed a deep red, he could feel them, and his dick was uncomfortable wet in his pants. 

Derek leaned down, kissed his forehead, and said, “Go.” 

He slowly stood on shaky legs, turned, and walked toward the door. He took a glance back, though, as he was leaving to see Derek curling himself around Samara. His cock, still sensitive from just having came, tried to twitch back to life, because, that, was almost more intimate than them fucking. 

Stiles made his way down the hallway, to their guest bathroom. His emotions are almost too much for him to deal with. There’s jealousy, and pain, and humiliation, but there’s also gratitude, and arousal, and contentment. It sounds crazy, he knows that it does, but he feels calm now -- a calmness that he hasn’t had since this whole kink began. 

He ends up sliding down against the wall, curling his knees up to his chest, and thumping his head back against the hard tile. He squeezes his eyes shut in an attempt to stop the tears stinging at the corners of his eyes. Because it does, it hurts. Derek loved it, loved fucking her. That wasn’t just a show for Stiles’ benefit. He’s never been this jealous in his life. He can feel it in every muscle, every nerve fiber, every cell of his skin -- this intense jealousy. He’s sick with it. He feels the bile in his throat. And, the only thing that hurts worse than knowing Derek fucked someone else, loved fucking someone else, is that fact that he wants him to do it again. If he could, if it wasn’t breaking a boundary, he’d go ask Derek to do it again right now -- even as he cried. He wondered why the hell he couldn’t have a fetish that wasn’t this fucking painful.

Even as he sat on the floor, sick to his stomach with jealousy; the images of Derek and Samara fucking played over, and over, in his head, and his cock started to harden again. 

 

After his little melt down, Stiles ended up in the living room waiting for them to come out. It wasn’t that long, not really, before he heard their bedroom door open and watched as Samara emerged, to his surprise, completely alone. She was disheveled, now; clothes wrinkled, makeup smeared, hair a mess, but still incredibly beautiful. Stiles stood up, and walked over to the armchair with her coat laying across it, and picked it up for her -- he held it out for her, and she smiled at him before sliding her arms into each of the sleeves. 

He didn’t expect her to say anything, because what was there to say? But, she did. She said, “Thank you for tonight.” 

“Oh, um” Stiles starts to stutter, but she keeps on. 

“Your boyfriend is amazing.” She says, walking towards the door, “That fucking dick he’s got, though.” 

It's crude, and Stiles probably shouldn’t be turned on by it, but he is, and his dick goes from the half chub he’s been sporting, practically, since he left the bathroom, to almost a full hard on. It’s uncomfortable, because he hasn’t been able to change his pants yet -- all his clothes in his and Derek’s closet. 

Samara notices, of course she does, and smirks at the still-wet patch on the front of his pants, “Maybe we can do this again sometime.” 

 

Once she’s gone, Stiles practically runs to his and Derek’s bedroom. Derek’s sprawled out on their bed, and he looks beautiful. He has sex hair, and his lips are smeared with lipstick, and he looks fucked out, and relaxed, and happy. 

“Holy fuck.” Stiles says, ripping his own clothes as Derek watches. He needs Derek right now, needs his cock in his ass, needs to cover every place that she touched with himself. 

Derek’s smiling, and raising up on the bed. He waits until Stiles is fully naked, aside from his stupid galaxy cat socks, and pulls him onto the bed. He manhandles Stiles until he’s in his lap, hands holding onto his ass. 

He gets serious as he asks, “Are you okay? I know that must’ve been a lot for you.”

Stiles can smell Samara’s cunt on his breath as he talks, and he groans, “Yes, yes, just fuck me, dammit.”

Derek, of course, doesn’t listen. He doesn’t roll Stiles over, and fuck him into the mattress like Stiles needs him to. Instead, he kisses him. Tongue pushing into his mouth, letting Stiles taste Samara on his tongue, and it has them both groaning. 

Derek is slow. He makes Stiles sit still in his lap, just kissing, for what feels like hours, and Stiles doesn’t understand. Doesn’t understand how Derek is this patient, and then it hits him. He’s just had sex. He doesn’t need to go again this soon; he’s fucked out, and satisfied. It’s Stiles who hasn’t had sex in five days, and who’s desperate. The heat of that curls in Stiles gut, and he decides that this is how he wants it forever; for himself to need Derek, and his cock, but Derek to be satisfied by other people, and still choose to keep fucking Stiles.

Eventually, far, far, too much later for Stiles’ taste, Derek is sliding the blue plug out of Stiles’ hole. It was big, and made his body stretch, and Stiles feels empty when it’s out. But, then, Derek is pushing at his lubed up, loose, hole with two fingers, and he feels better. Derek is always better than anything else. Derek, thankfully, takes pity on Stiles and makes fairly quick work of getting him ready.

And, then, Derek’s on top of him, just as he was with Samara a little bit ago, and he’s pushing his cock into his hole just like he did with her. It hits him how dirty this is, Derek fucking into him without even showering after her, but Stiles wouldn’t change a damn thing about it. 

He loves it; loves that he can see all the places she scratched him and makes sure to run his fingers over them, loves that he can see her lipstick on Derek’s mouth and wonders if it’s on his now, to, but most of all he loves sucking the areas of Derek’s skin where she made hickies. 

It’s a while before either of them come, but when they do it’s intense. They’re both loud, and gripping onto one another, and somehow spurts of Stiles’ come end up on the headboard, and Derek winds up collapsing onto him after he’s finished. 

He makes Derek get off, because jesus christ, sleeping with 200 pounds of werewolf on top of him doesn't sound like Stiles’ idea of a good time. Derek pulls him in tight, though, and kisses at the back of his ear. He’s sleepy, and sweet, and mumbles about how much he loves Stiles, and how good he was, until sleep finally takes over. 

As Stiles listens to Derek snore, he feels every human emotion that you can possibly feel all at once all because of one person. It’s intense, and overwhelming, and wonderful. It’s complex, and it’s beautiful, and Stiles has never felt this many things at once. Hell, he didn’t even think it was possible. He relishes in it, and understands, vaguely, that this is a unique human experience -- something many people don’t get to feel in their lifetimes.

He’ll share Derek for the rest of his life if it means he gets to have this feeling. And, he’ll love every second of it.

**Notes for the Chapter:**

> AND, FIN! 
> 
> At least, for now. I've decided to end this story here, as this feels like an ending, but may add to the verse later as I do still have some things that I'd like to explore with them. That'll probably be a while from now, though. 
> 
> If you enjoyed this fic, I would absolutely love to hear your feedback. And, I want to thank each and every one of you for reading.


End file.
